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Vinylidene chloride(CAS No. 75-35-4)

Vinylidene chloride C2H2Cl2 (cas 75-35-4) Molecular Structure

75-35-4 Structure

Identification and Related Records

【Name】
Vinylidene chloride
【CAS Registry number】
75-35-4
【Synonyms】
1,1-Dichloroethylene
1,1-dichloroethene single component*standard for
【EINECS(EC#)】
200-864-0
【Molecular Formula】
C2H2Cl2 (Products with the same molecular formula)
【Molecular Weight】
96.94
【Inchi】
InChI=1/C2H2Cl2/c1-2(3)4/h1H2
【InChIKey】
LGXVIGDEPROXKC-UHFFFAOYSA-N
【Canonical SMILES】
C=C(Cl)Cl
【MOL File】
75-35-4.mol

Chemical and Physical Properties

【Appearance】
colourless liquid
【Density】
1.218
【Melting Point】
-122℃
【Boiling Point】
31.2-31.7℃
【Vapour】
9.68 psi ( 20 °C)
【Refractive Index】
n20/D 1.426
【Flash Point】
-25℃
【Water】
moderate
【Solubilities】
moderate
【Color/Form】
Colorless liquid
Colorless liquid or gas (above 89 degrees F).
【Stability】
Stable. Very flammable - note low flash point. Vapour may travel considerable distances to a source of ignition. Incompatible with strong oxidizing agents, alcohols, halides, sopper, aluminium. Rapidly absorbs oxygen from the air and forms explosive peroxides. Light and water promote self-polymerisation. May form explosive mix
【Storage temp】
2-8°C
【Spectral properties】
MAX ABSORPTION (VAPOR): LESS THAN 200 NM
Index of refraction: 1.4249 at 20 deg C/D
IR: 11632 (Sadtler Research Laboratories Prism Collection)
NMR: 6385 (Sadtler Research Laboratories Spectral Collection)
UV: HBCP
MASS: 888 (NIST/EPA/MCDC Mass Spectral Database 1990 version); 203 (Atlas of Mass Spectral Data)
【Computed Properties】
Molecular Weight:96.94328 [g/mol]
Molecular Formula:C2H2Cl2
XLogP3-AA:2.3
H-Bond Donor:0
H-Bond Acceptor:0
Rotatable Bond Count:0
Exact Mass:95.953355
MonoIsotopic Mass:95.953355
Topological Polar Surface Area:0
Heavy Atom Count:4
Formal Charge:0
Complexity:27
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
F+:Extremelyflammable;Xn:Harmful;
【Risk Statements】
R12;R20;R40
【Safety Statements 】
S16;S29;S7
【HazardClass】
3
【Safety】
Hazard Codes:F+,Xn,T,F
Risk Statements:12-20-40-39/23/24/25-23/24/25-11
12:Extremely Flammable
20:Harmful by inhalation
40:Limited evidence of a carcinogenic effect
39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed
23/24/25:Toxic by inhalation, in contact with skin and if swallowed
11:Highly Flammable
Safety Statements:7-16-29-36/37-46-45
7:Keep container tightly closed
16:Keep away from sources of ignition - No smoking
29:Do not empty into drains
36/37:Wear suitable protective clothing and gloves
46:If swallowed, seek medical advice immediately and show this container or label
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR:UN 1303 3/PG 1
WGK Germany:3
HazardClass:3
PackingGroup:I
【PackingGroup 】
I
【Sensitive】
Light Sensitive
【Skin, Eye, and Respiratory Irritations】
Vapor is irritating to eyes, nose, and throat.
Skin contact with vinylidene chlorde causes irritation, which may partly be due to hydroquinone monomethyl ether inhibitor.
Inhalation may cause irritation or /CNS Depression/. Irritating to skin, eyes and respiratory system.
【Cleanup Methods】
Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, sawdust, or commercial sorbents. Apply appropriate foam to diminish vapor and fire hazard. /Vinylidene chloride, inhibited/
Water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Inject "universal" gelling agent to solidfy encircled spill & increase effectiveness of booms. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Vinylidene chloride, inhibited/
Air spill: Apply water spray or mist to knock down vapors. Combustion products include corrosive or toxic vapors. /Vinylidene chloride, inhibited/
Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Absorb in noncombustible material for proper disposal
【Transport】
UN 1303
【Fire Fighting Procedures】
Use dry chemical, foam, carbon dioxide, or water spray. Use water spray to keep fire-exposed containers cool. Use flooding quantities of water. Fight fire from protected location or maximum possible distance. /Vinylidene chloride, inhibited/
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Vinylidene chloride, inhibited/
Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Vinylidene chloride, inhibited/
Evacuation: If fire becomes uncontrollable, or container is exposed to direct flame--consider evacuation of one-half (1/2) mile radius. /Vinylidene chloride, inhibited/
【Fire Potential】
Flammable liquid
A very dangerous fire hazard when exposed to heat or flame.
【Formulations/Preparations】
Liquid grade
Grade: technical 95%, pure 99%, research.
【DOT Emergency Guidelines】
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Evacuation: Large spill: Consider initial downwind evacuation for at least 300 meters (1000 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or regular foam. Large fires: Water spray, fog or regular foam. Do not use straight streams. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
/GUIDE 130P: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Vinylidene chloride, inhibited; Vinylidene chloride, stabilized/
【Exposure Standards and Regulations】
Vinylidene chloride is an indirect food additive for use only as a component of adhesives.
【Reactivities and Incompatibilities】
At ambient temp, perchloryl fluoride is unreactive with 1,1-dichloroethylene, but reaction is explosive at 100-300 deg C, or if the mixture is ignited.
Condensation of trichlorotrifluoroethylene and 1,1-dichloroethylene at 180 deg C under pressure to give 1,1,2-trichloro-2,3,3-triflurorocyclobutane was effected smoothly several times in a 1 l autoclave. Scaling up to a 3 l preparation led to uncontrolled polymerization which distorted the larger autoclave.
Mixing vinylidene chloride & chlorosulfonic acid in a closed container caused the temp & pressure to increase.
Mixing vinylidene chloride & 70% nitric acid in a closed container caused the temp & pressure to increase.
Mixing oleum & vinylidene chloride in a closed container caused the temp & pressure to increase.
Aluminum, sunlight, air, copper, heat [Note: Polymerization may occur if exposed to oxidizers, chlorosulfonic acid, nitric acid, or oleum. Inhibitors such as the monomethyl ether of hydroquinone are added to prevent polymerization].
Reaction with ozone forms dangerous products.
Potentially explosive reaction with chlorotrifluoroethylene at 180 deg C. ... Explosive reaction with perchloryl fluoride when heated above 100 deg C.
Hazardous polymerization may occur. Usually contains inhibitors to prevent polymerization. Polymerization may be caused by elevated temperature, oxidizers, peroxide or air. Uninhibited monomer vapor may form polymer in vents and other confined spaces. May form organic peroxides following prolonged contact with air. May react with aluminum and its alloys.
【Other Preventative Measures】
The primary requirement for reduction of exposure to vinylidene chloride would be to limit emissions through improved housekeeping procedures in the industry.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personal hazard. Use water spray to knock down vapors. /Vinylidene chloride, inhibited/
Evacuation: If material leaking (not on fire) consider evacuation from downwind area based on amt of material spilled, location & weather conditions. /Vinylidene chloride, inhibited/
Personnel protection: ... Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Vinylidene chloride, inhibited/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet should be immediately removed due to its flammability hazard (i.e., for liquids with a flash point
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
【Protective Equipment and Clothing】
Goggles or face shield; rubber gloves and boots.
Wear appropriate chemical protective gloves, boots & goggles.
For 1,1-dichloroethylene some data (usually from immersion tests) suggesting break-through times greater than one hour are not likely for chlorinated polyethylene (CPE).
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
Respirator Recommendations: At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentrationl: Assigned Protection Factor (APF) Respirator Recommendation APF = 10,000 Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. APF = 10,000 Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 50 Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister/Any appropriate escape-type, self-contained breathing apparatus.
Wear full protective clothing and positive pressure self-contained breathing apparatus.
【Specification】

colourless liquid
Safety Statements:7-16-29-36/37-46-45
7:Keep container tightly closed
16:Keep away from sources of ignition - No smoking
29:Do not empty into drains
36/37:Wear suitable protective clothing and gloves
46:If swallowed, seek medical advice immediately and show this container or label
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
【Octanol/Water Partition Coefficient】
log Kow = 2.13
【Disposal Methods】
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers U078 and U029, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids. Also a potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. Also a potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds.
This compound should be susceptible to removal from waste water by air stripping.
The following wastewater treatment technologies have been investigated for 1,1-dichloroethylene: Concentration Process: Solvent extraction.
The following wastewater treatment technologies have been investigated for 1,1-dichloroethylene: Concentration Process: Stripping.
Environment Canada's Wastewater Technology Center operated a pilot plant at a landfill site to treat groundwater contaminated with volatile organic chemicals during the summer of 1986. The treatment system consisted of a packed air stripping column to treat the wastewater and two sequential granular activated carbon adsorbers to treat the off-gases. Among volatile organic chemicals in the wastewater were 1,1-dichloroethane, 1,2-dichloroethane, chloroform, 1,1-dichloroethylene, 1,1,1-trichloroethane, benzene, toluene, and trichloroethylene. Removal efficiencies varied from 27 to 99.9%. Optimal conditions, resulting in 94% removal of all volatile organic chemicals, were met with a 70:1 air-to-water ratio, a liquid flow rate of 4 l/min, and 1.3 cm Intalox saddles. Concentration of all compounds were below the lower detection limit of 2 ug/l in the effluent of the second granular activated carbon absorber.
An air stripping and incineration process is being used to clean a contaminated aquifer at McClellan Air Force Base. Groundwater is extracted and volatile organics are removed via a high-temperature air stripping system. Water soluble organics and some non-volatile organics are destroyed in a biological treatment unit. Volatile organics removed during air stripping are incinerated. Waste heat is recycled to preheat the air stripper water. Organic chemical concentrations are reduced from as high as 50 ppm to below detection limits.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Produced commercially by the dehydrochlorination of 1,1,2-trichloroethane by lime or sodium hydroxide & is extracted from the reactor by distillation, with the removal of oxygen to prevent polymerization. An azetropic distillation column is used to dry the monomer. The monomethyl ether of hydroquinone is added to commercial grades of vinylidene chloride as an inhibitor.
... Vinylidene chloride has been prepared from vinyl chloride by successive chlorination and dehydrochlorination steps ... .
Thermal dehydrochlorination of 1,1,1-trichloroethane (former commercial method).
Prepn from ethylene chloride: Reilly, US pat 2,140,548 (1938 to Dow.). By dechlorination of 1,1,2-trichloroethane: Conrad, Gould, US pat 2,989,570 (1961 to Ethyl Corp).
U.S. Exports

(1998) 1.979 billion pounds; (1999) 2.481 billion pounds
U.S. Imports

(1977) 1.63X10+7 G
(1982) 4.60X10+5 G
(1984) 1.81X10+7 g
(1986) 2.17X10+8 lb
(1998) 21 million pounds; (1999) 72 million pounds
U.S. Production

(1977) 9.1X10+10 G MIN-MAY INCL CAPTIVE PRODN
(1980) 7.8X10+10 G (EST, EXCL CAPTIVE PRODN)
(1985) 8.08X10+10 g (capacity)
An estimated 90700 tons/yr of the monomer were produced in the USA during the early 1980s.
>90,700 metric tons in 1982
1,1-Dichloroethene listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >100 million - 500 million 1990 >100 million - 500 million 1994 >10 million - 50 million 1998 >100 million - 500 million 2002 >10 million - 50 million
Consumption Patterns

Virtually all of the vinylidene chloride produced is used in the production of copolymers with vinyl chloride or acrylonitrile. A small percentage (4%) of vinylidene chloride is used as chemical intermediates (1985).
U.S. Demand: 68,000 tonnes in 1987; was projected to be 79,000 tonnes in 1992
Of all important chloroethanes and -ethylenes, vinylidene chloride has presently the smallest sales volume. Because of its unique applications in polymers for food containers, long-term demand will grow.
The annual production rate for the Western World amounts to about 150,000-200,000 tonnes, of which ca. 120,000 tonnes are used for poly(vinylidene chloride) and its copolymers. The rest is converted to 1,1,1-trichloroethane.
(1998) 14.029 billion pounds; (1999) 14.66 billion pounds; (2003) 17.82 billion pounds.
Polyvinyl chloride (PVC), 98 percent; miscellaneous, including copolymers with vinyl acetate, vinyl stearate and vinylidene chloride, and 1,1,1-trichloroethane, 2 percent.
【Sampling Procedures】
Sampling techniques using activated carbon adsorbent ... have been evaluated for determining vinylidene chloride in industrial atmospheres.
VINYLIDENE CHLORIDE HAS BEEN IDENTIFIED IN AIR BY TRAPPING IN PYRIDINE ... /USING AN IMPINGER/.

Biomedical Effects and Toxicity

【Pharmacological Action】
Vapor can cause dizziness and drunkenness; high levels cause anesthesia. Liquid irritates eyes and skin.
【Biomedical Effects and Toxicity】
1,1-DCE is rapidly absorbed following inhalation and oral exposures. Because of its low molecular weight and hydrophobic nature, dermal absorption is also likely ... . In rats treated with 1,1-DCE by gavage in corn oil, complete gastrointestinal absorption was found to occur at
As dose level of radioactive vinylidene chloride is incr in rats from 1-50 mg/kg body wt orally, or from 40-800 mg/cu m (10-200 ppm) by inhalation, the metabolic pathway becomes saturated, so that smaller percentage of dose admin is metabolized & more is eliminated via lung as vinylidene chloride. With the 1 mg/kg body wt oral dose & the 10 ppm inhalation dose, there was no difference in elimination by fed versus fasted rats. At 50 mg/kg body wt orally or 200 ppm by inhalation, there was significant incr in excretion of vinylidene chloride via lung & decr in urinary excretion of radioactivity in fed versus fasted rats. The main excretory route for (14)C-vinylidene chloride after intragastric, iv, or ip admin to rats is pulmonary: both unchanged vinylidene chloride & related carbon dioxide are excreted by that route; other VDC metabolites are eliminated via kidneys.
/In rats/ seventy-two hr after dose of 0.5, 5.0 & 50.0 mg/kg, 1.26, 9.70, 16.47% respectively, are exhaled as unchanged vinylidene chloride, & 13.64, 11.35, 6.13% as (14)C-carbon dioxide. Main pathway of elimination is through renal excretion with 43.55, 53.88, 42.11% of the admin radioactivity. Through the biliary system, 15.74, 14.54, 7.65% of the activity are eliminated. [REICHERT D ET AL; ARCH TOXICOL 42 (3): 159-69 (1979)] PubMed Abstract
... Single oral doses of (14)C-VDC /were admin/ by gavage to groups of 4 200 g male Alderley Park rats; excretion of radioactivity was followed for 72 hr: at 0.5 mg/kg, 0.7% was exhaled in the air as unchanged vinylidene chloride, 4.8% as (14)CO2; 80.2% was excreted in the urine. At 350 mg/kg, however, 67.3% was exhaled as unchanged vinylidene chloride & 1.0% as (14)CO2; 29.5% was excreted in the urine.
The absorption kinetics of 1,1-dichloroethylene (DCE) was studied in male Fischer 344 rats exposed to DCE atmosphere exposure system. Initial concentrations ranged up to 4000 ppm. The atmosphere of the exposure systems was analyzed every 10 minutes by gas/liquid chromatography. Chemical to air and tissue to air coeffiecients were estimated by a vital equilibration method. Tissues utilized in the partition experiments included blood, liver, muscle, and fat. The data were used to investigate metabolism kinetics of the compound. Uptake was adequately described by a single saturable metabolic pathway, and the metabolism was essentially abolished by pyrazole pretreatment. Maximum velocities of metabolism for the saturable pathways for 1,1-dichloroethylene was 27.2 moles per hour, calculated for a 225 gram rat. [Gargas ML et al; Toxicol Appl Pharmacol 86 (3): 341-52 (1986)] PubMed Abstract
A study of 1,1-dichloroethylene (1,1-DCE), was undertaken to contrast the kinetics of the chemical following iv injection with that following oral administration. Four dosage-levels of 1,1-dichloroethylene (10, 25, 50, and 100 mg/kg bw) in 50% aqueous polyethylene glycol 400 were given iv and po to fasted and nonfasted male Sprague-Dawley rats. Serial blood samples were taken from the tail artery of the lightly etherized animals for up to 490 min after dosing. The iv data revealed that disappearance of 1,1-dichloroethylene from the systemic circulation followed a triexponential pattern. Light ether anesthesia did not appear to alter the pharmacokinetics of iv injected 1,1-dichloroethylene. There was no difference between nonfasted and fasted iv rats in biological half-life or in any other pharmacokinetic parameter. Total body clearance, half-life, apparent volume of distribution and volume of distribution in the central compartment did show increases with increasing dose in these animals. Oral dosing experiments revealed that 1,1-dichloroethylene was absorbed very rapidly and completely from the gastrointestinal tract. Peak blood levels were reached 2 to 8 min following oral administration of 1,1-dichloroethylene as an aqueous suspension. The half-life of 1,1-dichloroethylene in orally dosed rats was somewhat longer than in their iv counterparts. The half-life values for nonfasted, orally dosed rats were longer than for their fasted counterparts, suggesting delayed absorption due to the presence of food. [Putcha L et al; Fundam Appl Toxicol 6 (2): 240-50 (1986)] PubMed Abstract
A physiologically based pharmacokinetic model has been developed for vinylidene chloride in the rat based on oxidative metabolism of vinylidene chloride and subsequent glutathione detoxification of metabolite. The model offers insight into the complex interrelationship between the processes of absorption, metabolism, and glutathione conjugation, and simulates the manner in which these factors operate in regulating vinylidene chloride toxicity. The physiologically based pharmacokinetics model successfully predicts blood, tissue, and exhaled air concentrations of vinylidene chloride, and liver glutathione levels as a function of dose and route of administration. The model also explains the complex dose-response mortality curves seen with vinylidene chloride. Because of the low blood:air partition coefficient of vinylidene chloride and its saturable metabolism, the amount of vinylidene chloride dose that is metabolized is sensitive to the rate of absorption. After an intravenous bolus dose, most of the administered vinylidene chloride is exhaled unchanged within a few minutes. Blood vinylidene chloride half-life is not representative of metabolism rates but to reequilibration of vinylidene chloride from fat. Rats with greater fat content, therefore, display longer vinylidene chloride blood half-lives. [D'Souza RW, Anderson ME; Toxicol Appl Pharmacol 95 (2): 230-40 (1988)] PubMed Abstract
In rats and mice, vinylidene chloride is very quickly absorbed after oral administration; in mice, elimination is tri-exponential...
1,1-DCE is rapidly absorbed following inhalation and oral exposures. Because of its low relative molecular mass and hydrophobic nature, dermal absorption is also likely ... . In rats treated with 1,1-DCE by gavage in corn oil, complete gastrointestinal absorption occurs at
The major route of excretion for unchanged 1,1-DCE is through the lungs ... . The majority of the 1,1-DCE, however, is rapidly metabolized to non-volatile compounds and covalently bound derivatives ... . In both animal and human tissue, CYP2E1 catalyses the initial oxidation of 1,1-DCE ... .. The covalent binding and cellular damage in kidney, lung, and liver correlate with the high concentration of CYP2E1 in certain cell populations in these tissues ... . Mice metabolize more 1,1-DCE than rats. For example, when given 50 mg/kg body weight by oral gavage in corn oil, mice excrete 6% and rats excrete 28% of the dose as unchanged 1,1-DCE through the lungs ... . When exposed to 40 mg/cu m by inhalation for a single 6-hr period, mice excrete 0.65% and rats excrete 1.63% of the absorbed dose as unchanged 1,1-DCE through the lungs ... . Intraperitoneal administration of (14C)-1,1-DCE at 125 mg/kg body weight to mice resulted in the highest concentrations of covalent binding (based on protein content) in the kidney, lung, and liver...
The oxidative metabolism of 1,1-DCE reaches saturation in rats at an oral exposure of 10 to 50 mg/kg body weight and an inhalation exposure of 790 mg/cu m ... . Because 1,1-DCE is lipophilic and has a blood-to-air partition coefficient of 5 in rats ... , any 1,1-DCE not metabolized following oral or inhalation exposure is rapidly exhaled unchanged when exposure is terminated. Based on its low octanol/water partition coefficient, 1,1-DCE will not bioaccumulate in tissues to any significant extent.
Vinylidene chloride is exhaled in human breath following inhalation exposure. Breath from student volunteers ... was sampled using a spirometer as the subjects inhaled pure air. The ratio of vinylidene chloride in the breath to that in pre-exposure air was 0.78 +/-86 (n = 15). A significant Spearman correlation coefficient of 0.77 was determined between air and breath levels of vinylidene chloride in 17 human subjects. The following log-linear model was capable of giving a reasonable prediction of breath levels from the preceding 8-hr air exposure levels: log concentration in breath (ug/cu m) = 0.24 +/- 0.67 + (0.71 +/- 0.17) log concentration in air (ug/cu m). The authors suggested that, if these observations were confirmed, recent exposures and body burdens of individuals could be estimated from breath analysis. However, this may be hampered by biphasic elimination as reported for animals.
The uptake, disposition, and respiratory elimination of 1,1-dichloroethylene (1,1-DCE) during inhalation exposure were evaluated to gain insight into the pharmacodynamics of the halocarbon. Anesthetized male Sprague-Dawley rats inhaled 25, 75, 150, or 300 ppm 1,1-DCE for 3 hr from an aluminized Mylar bag through a miniaturized one-way breathing valve inserted into the trachea. Periodic air samples were taken immediately adjacent to the valve from the separate inhaled air and exhaled breath streams concurrently with blood samples from a cannulated femoral vein and analyzed for 1,1-DCE content by gas chromatography. 1,1-DCE was absorbed very rapidly, in that substantial levels were present in the venous blood at the first sampling time (ie, 2 min). Percentage systemic uptake decreased over time after initiation of exposure until equilibrium was established. Percentage uptake after reaching equilibrium varied inversely with the exposure concentration. 1,1-DCE venous whole-blood levels in animals exposed to 25, 75, and 150 ppm 1,1-DCE increased rapidly to near steady state within approximately 45 min, as did concentrations of 1,1-DCE in the exhaled breath and alveolar air. Calculation of the amount of 1,1-DCE taken up by the body over the course of the 3-hr exposures revealed that cumulative uptake of the inhaled chemical was statistically linear for the 25-, 75-, and 150-ppm exposures. Accumulation plots for 300-ppm exposed animals, however, were best fitted to a cubic curve form. Although trends toward the establishment of equilibrium were initially seen in the 300-ppm exposed animals, levels of 1,1-DCE in the blood and breath rose progressively during the latter hour of the 3-hr exposure period. Thus, despite increased exhalation of 1,1-DCE, these animals could not prevent systemic accumulation of the chemical. [Dallas CE et al; Toxicol Appl Pharmacol 68 (1): 140-51 (1983).] PubMed Abstract
... A study of ... 1,1-dichloroethylene (1,1-DCE), was undertaken to contrast the kinetics of the chemical following iv injection with that following oral administration. Four dosage-levels of 1,1-DCE (10, 25, 50, and 100 mg/kg BW) in 50% aqueous polyethylene glycol 400 were given iv and po to fasted and nonfasted male Sprague-Dawley rats. Serial blood samples were taken from the tail artery of the lightly etherized animals for up to 490 min after dosing. 1,1-DCE concentrations in the whole blood were determined by gas chromatographic head-space analysis. Evaluation of the iv data revealed that disappearance of 1,1-DCE from the systemic circulation followed a triexponential pattern. Light ether anesthesia did not appear to alter the pharmacokinetics of iv-injected 1,1-DCE. There was no difference between nonfasted and fasted iv rats in ... any ... pharmacokinetic parameter. Total body clearance, t1/2, apparent volume of distribution and volume of distribution in the central compartment did show increases with increasing dose in these animals. Oral dosing experiments revealed that 1,1-DCE was absorbed very rapidly and completely from the G.I. tract. Peak blood levels were reached 2 to 8 min following oral administration of 1,1-DCE as an aqueous suspension. ... Bioavailability of 1,1-DCE, as determined by comparing areas under blood concentration versus time curves (AUCs), was equivalent in animals given the same dose of 1,1-DCE iv and po. AUCs increased with increasing dose in iv and po groups, but the increases were not proportional to dose. [Putcha L et al; Fundam Appl Toxicol 6 (2): 240-50 (1986).] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
The rate constant for the vapor-phase reaction of 1,1-dichloroethylene with photochemically-produced hydroxyl radicals is 1.09X10-11 cu cm/molecule-sec at 25 deg C(1). This corresponds to an atmospheric half-life of about 1.5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 1,1-dichloroethylene with ozone has been measured as 3.98X10-21 cu cm/molecule-sec at 25 deg C(2). This corresponds to an atmospheric half-life of about 7.9 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(3). The rate constant for the vapor-phase reaction of 1,1-dichloroethylene with photochemically-produced nitrate radicals has been measured as 1.23X10-15 cu cm/molecule-sec at 25 deg C(4). This corresponds to an atmospheric half-life of about 27 days at an atmospheric concentration of 2.4X10+8 nitrate radicals per cu cm(5).
Under photochemical smog situations with nitrogen dioxide present, 1,1-dichloroethylene decomposes rapidly (half-life

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